Synthesis of α-D-idoseptanosyl glycosides using an S-phenyl septanoside donor

被引：38

作者：

Castro, S

Fyvie, WS

Hatcher, SA

Peczuh, MW

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 21期

关键词：

D O I：

10.1021/ol051912e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An S-phenyl alpha-D-idoseptanoside donor was used in the selective preparation of a series of alpha-D-idoseptanosyl glycosides. Glycosylation of a methyl beta-D-glycero-D-guloseptanoside acceptor with the new donor constituted the first synthesis of a septanose disaccharide.

引用

收藏

页码：4709 / 4712

页数：4

相关论文

共 18 条

[1] Act natural [J].

Benner, SA .

NATURE, 2003, 421 (6919) :118-118

[2] Recognition of septanose carbohydrates by concanavalin A [J].

Castro, S ;

Duff, M ;

Snyder, NL ;

Morton, M ;

Kumar, CV ;

Peezuh, MW .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (21) :3869-3872

[3] Recent developments in oligosaccharide synthesis [J].

Davis, BG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (14) :2137-2160

[4] Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF3•Et2O [J].

Debenham, SD ;

Toone, EJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (02) :385-387

[5] Septanose carbohydrates:: Synthesis and conformational studies of methyl α-D-glycero-D-idoseptanoside and methyl β-D-glycero-D-guloseptanoside [J].

DeMatteo, MP ;

Snyder, NL ;

Morton, M ;

Baldisseri, DM ;

Hadad, CM ;

Peczuh, MW .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :24-38

[6] Divergent synthesis and biological activities of lipid A analogues of shorter acyl chains [J].

Fukase, K ;

Fukase, Y ;

Oikawa, M ;

Liu, WC ;

Suda, Y ;

Kusumoto, S .

TETRAHEDRON, 1998, 54 (16) :4033-4050

[7] 2,3-anhydro sugars in glycoside bond synthesis.: Highly stereoselective syntheses of oligosaccharides containing α- and β-arabinofuranosyl linkages [J].

Gadikota, RR ;

Callam, CS ;

Wagner, T ;

Del Fraino, B ;

Lowary, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4155-4165

[8] Carbohydrate-based mimetics in drug design: Sugar amino acids and carbohydrate scaffolds [J].

Gruner, SAW ;

Locardi, E ;

Lohof, E ;

Kessler, H .

CHEMICAL REVIEWS, 2002, 102 (02) :491-514

[9] The first synthesis of substituted azepanes mimicking monosaccharides:: a new class of potent glycosidase inhibitors [J].

Li, HQ ;

Blériot, Y ;

Chantereau, C ;

Mallet, JM ;

Sollogoub, M ;

Zhang, YM ;

Rodríguez-García, E ;

Vogel, P ;

Jiménez-Barbero, J ;

Sinaÿ, P .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (10) :1492-1499

[10] STEREOSELECTIVE RING-CLEAVAGE OF 3-O-BENZYL-4,6-O-BENZYLIDENEHEXOPYRANOSIDE AND 2,3-DI-O-BENZYL-4,6-O-BENZYLIDENEHEXOPYRANOSIDE DERIVATIVES WITH LIALH4-ALCL3 REAGENT [J].

LIPTAK, A ;

JODAL, I ;

NANASI, P .

CARBOHYDRATE RESEARCH, 1975, 44 (01) :1-11